Molecular Recognition in Proton Transfer Compounds of Brucine with Achiral Substituted Salicylic Acid Analogues
Smith, Graham, Wermuth, Urs D., Healy, Peter J., & White, Jonathan M. (2006) Molecular Recognition in Proton Transfer Compounds of Brucine with Achiral Substituted Salicylic Acid Analogues. Australian Journal of Chemistry, 59(5), p. 328.
The 1:1 proton-transfer brucinium compounds from the reaction of the alkaloid brucine with 5-nitrosalicylic acid, 3,5-dinitrosalicylic acid, and 5-sulfosalicylic acid, namely anhydrous brucinium 5-nitrosalicylate (1), brucinium 3,5-dinitrosalicylate monohydrate (2), and brucinium 5-sulfosalicylate trihydrate (3) have been prepared and their crystal structures determined by X-ray crystallography. All structures further demonstrate the selectivity of brucine for meta-substituted benzoic acids and comprise three-dimensional hydrogen-bonded framework polymers. Two of the compounds (1 and 3) have the previously described undulating brucine sheet host-substructures which incorporate interstitially hydrogen-bonded salicylate anion guest species and additionally in 3 the water molecules of solvation. The structure of 2 differs in having a three-centre brucinium–salicylate anion bidentate N+–H···O(carboxyl) hydrogenbonding association linking the species through interstitial associations involving also the water molecules of solvation. A review of the crystallographic structural literature on strychnine and brucine is also given.
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|Item Type:||Journal Article|
|Subjects:||Australian and New Zealand Standard Research Classification > CHEMICAL SCIENCE (030000)|
|Divisions:||Past > QUT Faculties & Divisions > Faculty of Science and Technology|
|Copyright Owner:||Copyright 2006 CSIRO Publishing|
|Copyright Statement:||Reproduced in accordance with the copyright policy of the publisher.|
|Deposited On:||12 Jan 2007|
|Last Modified:||29 Feb 2012 23:26|
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